Combination of organic acids.



UNITED TNT OFFICE.

ALEX B. DAVIS, 01? INDIANAPOLIS, INDIANA, ASSIGNOR TO THE ELI LILLY AND COMPANY, OF INDIANAPOLIS, INDIANA, A CORPORATION OF INDIANA.

COMBINATION OF ORGANIC ACIDS.

No Drawing.

Specification of Letters Patent. Patented 04 31], 31, 1916.

Application filed July 26, 1915. Serial No. 41,908.

T 0 all whom it may concern:

Be it known that I, ALEX B. DAVIS, a citizen of the United States, residing at Indianapolis, MIarion county, and State of Indiana,

have invented and discovered certain new 0 and useful Improvements in Combinations of Organic Acids of which the followim is l a. specification. a i

My invention relates to an ester of sali- I l t l cylic acid and Q-phenyl-quinolin-et-carb0X-- l ylic acid. The compound is a valuable therapeutic agent. It is produced by treating a solution of salicylic acid with the chlorid of 2-phenyl-quinolin--carboxylic acid either with or without the addition of a tertiary base. The preparation may be made as follows:

2 phenyl quinolin 4: carboxylic acid is acid and salicylic acid.

2. An ester of salicylic acid and Q-phenylquinolin-A-carboxylic acid.

3. A compound of the formula treated with somewhat more than one molec- 0 ular proportion of thionyl chlorid of the l formula SOCl Sulfur dioxid escapes and the hydrochlorid of the acid chlorid of the formula 0 K I I a... /v 4. The process of treating a quinolini- I carbkoxylig 1withhtifinyl cfillillorid and I Tlig pibd s s f irodui ii i g ester of salicylic acid with 2-phenyl-quinolinAc-carboxylic acid by treating 2-phenyl-quinolin-4- carboxylic acid with thionyl chlorid and combining the resulting chlorid with salicylic acid.

6. The process of producing compounds of Q-phenyl-quinolin-l-carboxylic acid and salicylic acid which consists in forming the chlorid of 2-phenyl-quinolin-e-carboxylic acid and combining this with salicylic acid.

In witness whereof, I have hereunto set my hand and seal at Indianapolis, Indiana, this 21st day of July, A. D. nineteen hundred and fifteen.

ALEX B. DAVIS.

Witnesses:

A. C. Bron, E. C. CLEMENTS.

remains as a yellow mass. This is broken up, suspended in dry benzol, an equimolecular proportion of salicylic acid added and the mass boiled under a reflux condenser several hours. The benzol is then evaporated, the resulting yellow mass treated with water, filtered, washed, dried and ground to a powder.

The ester may also be made as follows: The quinolin acid chlorid is suspended in benzol, an equimolecular proportion of salicycle acid added and then somewhat more than one molecular proportion of pyridin or some other tertiary base which can take up the hydrochloric acid liberated during esterification. The mass is boiled a short time under a reflux condenser, the benzol evap- Genie: of this patent may be obtained to: five cents each, by addressing the ecmmtssioner of Patents,

1 Washington, I). 1;. 

